Built for General Patton to sail around the world

Say the word, and a captain and the boat are yours, from 90 minutes to a full day

Or book a seat on one of our shared experiences

Wherever the wind may blow

Marblehead

Gloucester

Manchester

and beyond...

Sunset Sail Salem

Let us be your Salem, MA sailing experience. We offer private charters and shared experiences for day sails and sunset cruises on beautiful, historic Salem Sound. Take in the views of Boston’s North Shore, scenic islands, and plenty of wildlife to look out for as the water laps against the hull and wind fills the sails.

From carefully planned special occasions to a spontaneous trip out on the water to escape the summer heat, Sunset Sail Salem is your perfect North Shore sailing experience.

Two beautiful yachts

Our lovely private charter Friendship Sloop Wenonah returns to Salem, MA this Summer with Owner/Operator Captain Eric Turner at the helm. A beautifully restored 1970s classic with a rich history on Boston’s North Shore, Wenonah runs private sailing trips for up to 6 people.

Historic schooner When And If, built for General George S Patton takes up residence with Sunset Sail Salem under the care of Captain Dylan Salzmann this Summer. A stunning 1939 custom Alden design for truly glorious sailing with room for up to 28 guests as a shared experience or for a private sail.

Your dream sail come true

Book a seat to enjoy a shared sail scheduled on the beautiful When and If, sailing every day this Summer.

The beauty of truly flexible service: For something more tailor-made, look to a private charter on Wenonah. Sunrise or Full Moon, 90 minutes or an all-day adventure: an unforgettable private experience for you and your 5 guests.

Planning a larger party or a special occasion? When and If is yours to command for a breathtaking private charter for up to 28 people.

We are a small group of sailors who want to share the magic of these beautiful boats with you, and we’ll do everything we can to make your dream sail come true.

August 11th & 12th: A superb opportunity to race When And If with a host of other yachts her perfect match in speed, caliber and beauty. Prepare yourself for a full day sailing, sightseeing, racing and relaxing as we head to Marblehead for this highlight of the Summer yachting season. Tickets include sailing to and from Marblehead, a light race lunch and as much competitive classic sailing as you can handle with spectacular views not to be missed! One or two-day tickets available, here.

Meet our beautiful classic yachts…

Friendship Sloop WenonahSail a New England Classic

Whether you prefer sailing for 90 minutes, 2 hours, half the day or a full day, Friendship Sloop Wenonah is perfect for your private sailing party because every charter is a private charter.

See the local area’s coast, rich in maritime history, the way seafarers did over a century ago on a classic, traditionally rigged Friendship sloop departing daily from Pickering Wharf Marina in downtown Salem. Whether it be for a family outing, romantic getaway, or a fun day with good friends, join us for a classic New England sailing experience.

Schooner When And IfThe historic ship built for General George Patton

General George Patton said: “When the war is over, and If I live through it, Bea and I are going to sail around the world.” This magnificent vessel is the peacetime dream of an American war icon, and she was launched with her name full of hope and ambition precluding a destiny as yet unfulfilled.

The fame of this ship arises from her historical provenance and her heartwarming beauty: the meeting of minds between a great military figure and America’s premier naval architect of the time.

Come and be part of her present story! Help raise sail, take a turn at the helm or simply relax and enjoy the gorgeous New England scenery as we harness the fresh summer breezes of Salem Sound and enjoy a trip out on the water.

New for Summer 2018

Historic Schooner When And If

George Patton’s historic schooner yacht, proud to be a guest of Sunset Sail Salem for summer 2018